An Efficient and Practical Chemoenzymatic Route to (3R,3aR,6R,6aR)-Hexahydrofuro[3,2-b]furan-6-amino-3-ol (6-Aminoisomannide) from Renewable Sources

Abstract

The synthesis of 6-aminoisomannide is easily achieved starting from the renewable, inexpensive, and commercially available isosorbide in 66% overall yield. A biocatalyzed highly regioselective acetylation of the 3-endo hydroxyl group of isosorbide was followed by the stereospecific interconversion of the 6-exo hydroxyl group into an azido group, through reaction with trifluoromethanesulfonic anhydride, followed by nucleophilic displacement of the triflate group by sodium azide. Finally, reduction of the azido group and deacetylation of the 3-hydroxy group were performed in one pot using LiAlH₄.

Key words

isomannide - isosorbide - chiral amino alcohols - supported enzyme - lipase

Publication History

Received: 01 May 2021

Accepted after revision: 27 May 2021

Accepted Manuscript online:
21 June 2021

Article published online:
06 July 2021

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